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Communication

4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline

1
Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
2
Center for Drug Design, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Stanislav Kafka
Molbank 2021, 2021(4), M1305; https://doi.org/10.3390/M1305
Received: 21 October 2021 / Revised: 1 December 2021 / Accepted: 2 December 2021 / Published: 9 December 2021
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, we demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation. View Full-Text
Keywords: nitrogen heterocycles; thiazoloquinoline; 1,3-dipolar cycloaddition; Pd-catalyzed carbonylation; quinoline-N-oxide nitrogen heterocycles; thiazoloquinoline; 1,3-dipolar cycloaddition; Pd-catalyzed carbonylation; quinoline-N-oxide
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MDPI and ACS Style

Larson, P.G.; Ferguson, D.M. 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline. Molbank 2021, 2021, M1305. https://doi.org/10.3390/M1305

AMA Style

Larson PG, Ferguson DM. 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline. Molbank. 2021; 2021(4):M1305. https://doi.org/10.3390/M1305

Chicago/Turabian Style

Larson, Peter G., and David M. Ferguson. 2021. "4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline" Molbank 2021, no. 4: M1305. https://doi.org/10.3390/M1305

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